HCID 131731232, compound → HCID 131731231, compound

HRID 1182875Notes

Reaction equation

HRID 1182875 reaction equation
[CH2:1]1[CH2:34][O:33][C:3]2([CH2:24][CH2:23][C@@:22]3([CH3:25])[C:5](=[CH:6][C:7](=[O:30])[C@@H:8]4[C@@H:21]3[CH2:20][CH2:19][C@@:13]3([C:14]([CH3:18])([CH3:17])[O:15][SiH3:16])[C@H:9]4[CH2:10][CH2:11][C@@H:12]3[C:26]([CH3:29])([CH3:28])[CH3:27])[C:4]2([CH3:32])[CH3:31])[O:2]1>O1CCOCC1.[Pd]>[CH2:34]1[CH2:1][O:2][C:3]2([CH2:24][CH2:23][C@@:22]3([CH3:25])[CH:5]([CH2:6][C:7](=[O:30])[C@@H:8]4[C@@H:21]3[CH2:20][CH2:19][C@@:13]3([C:14]([CH3:17])([CH3:18])[O:15][SiH3:16])[C@H:9]4[CH2:10][CH2:11][C@@H:12]3[C:26]([CH3:29])([CH3:28])[CH3:27])[C:4]2([CH3:32])[CH3:31])[O:33]1

Participants

4

Reactant 1

HCID 131731232HCID 131731232, compound

Product 1

HCID 131731231HCID 131731231, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,3-(ethylenedioxy)-4,4-dimethyl-17β-tert-butyldimethyl-silyloxyandrost-5-en-7-one (3.9 g) in dioxane (270 ml), Pd/C 10% (390 mg) was added, and then the mixture was hydrogenated at RT for 72 h. The catalyst was filtered off, washed with EtOAc and the organic phase evaporated under reduced pressure. The crude reaction mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc/toluene 90/5/5) to give 3,3-(ethylenedioxy)-4,4-dimethyl-17β-tert-butyldimethyl-silyloxyandrostan-7-one (2.44 g, 63% yield).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with EtOAc
  3. customthe organic phase evaporated under reduced pressure
  4. customThe crude reaction mixture
  5. customwas purified by flash chromatography (SiO2, n-hexane/EtOAc/toluene 90/5/5)

Sources & evidence

ORD record
ord-65fbc74d1f774a319f99937e51ecfac8
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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